Kim Kardashian Booed at Tom Brady Roast Before Comparing Him to Caitlyn Jenner

The audience may have booed Kim Kardashian when she first got on stage at The Roast of Tom Brady — but she got the last laugh with jokes about their alleged romantic past, her stepdad, Caitlyn Jenner, and O.J. Simpson.

After Kevin Hart called Kardashian to the stage from her table in the crowd to make a “special toast” on Sunday, May 5, attendees at the live roast started to boo her. While she attempted to go into her joke about Hart, the boos were too loud.

“Alright, alright,” she said.

Several seconds later, the reality star was able to begin.

“I wasn’t going to come tonight, but since I’m not here as Tom’s date, there’s still a good chance I might,” Kardashian said, making her first reference to the rumors that she and the quarterback dated.

She continued by making a reference to her infamous 2007 sex tape: “Speaking of Tom and I dating, I know there were some rumors that we were and I’d never say if we did or not, I’d just release the tape.”

Kardashian and Brady were linked in spring 2023 following his split from Gisele Bündchen. After sources denied dating rumors, they were seen together at a Michael Rubin’s star-studded party in the Hamptons that July.

During the toast, Kardashian joked that things would “never work out” between the twosome — going on to compare Brady to her stepdad, Jenner, who transitioned in 2015.

“But I do know it would never work out. An ex-athlete, high cheek bones, slinky hair — you remind me too much of my stepdad now.” Kardashian quipped. “Part of me thinks you would try to undress me, just to try on my clothes. I know the transition from the NFL must have been really hard, but I think my stepdad is a great example from you. She’s one of the greatest athletes in the world who’s proved you can do anything in this next chapter. You can become a commentator, a far right Republican, or even a strong, confident woman.”

Kardashian’s three-minute cameo wouldn’t be complete without a reference to O.J. Simpson.

“Honestly, it’s hard for me to watch people roast you, but I think enough of my family members have defended former football players,” she said, referring to dad Robert Kardashian Sr., who represented Simpson in his high-profile murder trial of ex-wife Nicole Brown Simpson.

The audience was on Kardashian’s side by the time she made the O.J. joke, which comes one month after he died at 76 after a battle of cancer.

“So I’m just here tonight to support you and celebrate you,” Kardashian said before comparing retirement to a breakup. “I’ll give you the same advice I give all of my exes, goos luck knowing the best is behind you.”

The Roast of Tom Brady continues live on Netflix.